Water → Carbamic acid, [1-(methoxymethyl)cyclopentyl]-, phenylmethyl ester

HRID 855866Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:18])[NH:10][C:11]1([CH2:16][OH:17])[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H+].[B-](F)(F)(F)F.[Si](C=[N+]=[N-])(C)(C)[CH3:26].O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:18])[NH:10][C:11]1([CH2:16][O:17][CH3:26])[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold solution (0° C.) of (1-hydroxymethyl-cyclopentyl)-carbamic acid benzyl ester (250 mg, 1 mmol) and 48% aqueous HBF4 (0.13 ml, 1 mmol) in CH2Cl2 (4 mL) was added TMSCHN2 (2N in hexane, 2 mL, 4 mmol) via syringe. The resulting mixture was stirred, at 0° C., for ½ hour followed by the addition of water (10 mL). The aqueous mixture was extracted with CH2Cl2 (2×50 mL), and the combined organic layers were dried (sodium sulfate), filtered, concentrated and chromatographed with 30% ethyl acetate/hexane to provide the titled compound. MS (DCI) m/e 264 (M+H)+.

Workup

extractionThe aqueous mixture was extracted with CH2Cl2 (2×50 mL)
dry with materialthe combined organic layers were dried (sodium sulfate)
filtrationfiltered
concentrationconcentrated
customchromatographed with 30% ethyl acetate/hexane

Sources & evidence

ORD record: ord-4c6a9e6f3c9648f79aea6a8696e889c3
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262207B2

Reaction notes

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